New azo dyestuffs



2o benzene,

MYRTIL KAHN, OF COLOGNE, GERMANY, ASSIGNOR TO GENERAL AN ILIN E WORKS, INO., I

OF NEW. YORK, N. Y., A CORPORATION OF Patented June 3,

UNITED STATES} PATENT; OFFICELY DELAWARE NEW AZO DYESTUFES No Drawing. Application filed September lO, 1927, Serial No. 218,860, and in Germany October 22, 1926.

The present invention concerns new azo dyestufl's. They are obtained by combining the tetrazo compounds of the intermediate bodies from a p-cliamine and an amino-naphthol sulfonic acid with two molecules of a 1 hydroxyalkylamino 3 amino-benzene or with one molecule of the same and an desired component, the sequence of the com, ination being immaterial.

In accordance with the invention az o dyestufi's possessing, remarkably good dyeing properties coupled with good solubility are obtained. It is only necessary thatone hydroxy alkyl group e. g. a hydroxy ethyl group be present in the whole dyestuff molecule, in order .to produce the required solubility. The hydroxy alkyl compounds are easily prepared from the corresponding diamines an chloro substituted alcohols. Thus,

for example, 1-hydroxy-ethylaminmB-aminois readily obtained by warming together in aqueous solution, one molecule of. m-phenylenediamine, one molecule of chloroethyl alcohol and a quantity of sodium carbonate,

The resulting solution can be used directly for the manufacture of the dyestuffs.

The new products are generally in the form v of their alkali metal salts dark powders solu ble in water and in concentrated sulfurici acid with a blue-black coloration dyeing cotton from blue to black shades, being split up by treatment with stannous chloride and hydrochloric acid into a para-diaminc, a di-' aminonaphthol sulfonic acid and an oxy alkyl triaminobenzene. They have most probably the'formula II $505119 l N=NR1 wherein R represents an aryl radicle, R an azodyestufi component, X hydrogen or a sulfonic group, R stands for one-of the substituents CH .CH and CH .CH.QH

being in the form of their alkali metal salts in alkali and cooled, treated with hydrochloric acid until an acid reaction with Congo paper is obtained and then converted into the tetrazo compound by the addition of a solution of 10 parts by weight of sodium nitrite. 11 parts by weight of a l-hydroxy-ethyl- -amino-3-aminobenzcnc, obtained as above indicated arev caused to combine withflthe tetrazo compound, the whole being neutralgradual addition of sodium carized by the portion on paper bonate solution until a test proves the'disappearance of the tetrazo compound and the diaminc. Thereupon a solution of 8 parts by weight of m-phenylene diamine and excess of sodium carbonate are added. After stirring for severabhours the resulting product is filtered and dried. The

new dyestuif dyes vegetable fibres in deep black shades; It has most probably the fol-,

lowing formula-:-

and is a dark powder soluble in waterand in concentrated sulfuric acid with a blue-black coloration yielding upon reduction with stannous chloride and hydrochloric acid paraphenylenediamine, 1.3.4.-triaminobenzene, 1

2.7-diamino-8-naphthol-6-sulfonic acid.

Other p-diamines such for example as beni H hydroxy-ethylamin0-3.4-diaminobenzene and I amines; instead of 2'-amino-8-naphtho1 -6-.

sulphonic acid other aminonaphtholsulphonic acids may be used, such for example as. 2.5-

1 aminonaphthol-7-sulphonic acidand the like ylaminoi-amino-benzene of the iormula:

insteafl of hydroxy ethyl m-phenylenediamine other similar diamines may be used,- such for exampleas 1-methyl-2-hydroxy-eth NH. CHLCHI.OH

glyceryl-m-phenylene-diamine of the following formula nncmc momcmon epichlorhydrin) and the like.

I claim v v 1. The process for the production-of new azo dyestufis cxilmprising coupling the tetrazo l e intermediate bodies from'a compound of t an amino naphthol sulfonic p-diamine and acid with two molecules of components at least one of them being a l-hydroxy-alkylamino-3-aminobenzene, the sequence of the combination bein immaterial.

2. As new products the azodyestufis having most probably the formula andbeing a dark powder soluble in water and in concentrated sulfuric acid with a blueblack coloration, yielding upon reduction with stannous chloride and hydrochloric acid para phenylenediamine, 1.2.4 triaminoben zene 2.7-diamino-8-naphthol-6-sulfonic acid and l-oxyethyl-amino3.4-diaminobenzene.

' In testimony whereof'I have hereuntoset my hand. MYRTIL KAHN.

(obtained from m-phenylene diamine and wherein R represents an aryl radicle, R an azodyestuff component, X hydrogen or a sul- 3. Asa new product the dyehair'ing the formula N= @Nncimon M 

